At the start of every offseason, NFL organizations must decide which of their pending free agents or players entering their contract year the team will attempt to re-sign before free agency begins, let test the market but hope to re-sign later, and which to let walk.
At times, the decision will be obvious. Over the past several years, most expected that the team would try to re-sign (and likely succeed in re-signing) George Kittle, Deebo Samuel, Fred Warner, Nick Bosa, and Brandon Aiyuk. This past offseason, the only questions surrounding Brock Purdy's extension were when and for how much.
This past year, the 49ers were proactive in releasing players, but there were clearly some they wanted to keep. They were hoping to re-sign Dre Greenlaw and Talanoa Hufanga but were unable to do so, despite making a heroic effort to bring back the former. The team would like to have retained Charvarious Ward, but he had made clear he would not return due to the emotional trauma he suffered when his daughter died. There was no bad blood between him and the team, just the knowledge that the tragedy was associated with Northern California, and he understandably could not stay.
This coming season is the contract year for several players, a number of them starters. Let's look at who they are and what the Niners should do.
WR Jauan Jennings
Jauan Jennings has been one of the best wide receiver bargains in the NFL since he was selected in the 7th round of the 2020 draft out of Tennessee. Over the following five seasons, the 49ers paid him just $10.5 million. This year, the second of a two-year extension, he will make a little over $4 million. Last season, he finished with 975 yards, but would undoubtedly have topped 1,000 if not for a bogus ejection in the final game. As it was, he still finished with more yards than DJ Moore, who makes an average of $27.5 million per year, and roughly the same as DK Metcalf, who just signed a new deal with Pittsburgh that averages over $30 million annually.
The Niners should prioritize re-signing Jennings and attempt to finalize a deal before the end of the season. Jennings has been a key component of the offense the past few years and was invaluable last year when Brandon Aiyuk went down. No one knows how the latter will perform when he returns this year, but that should not affect the team's approach. Even if Aiyuk returns to his pre-injury All-Pro form, he will count 41 million against the cap in 2027, a number that will certainly be reduced either by restructuring the contract or releasing or trading him.
Considering Ricky Pearsall will be on his rookie contract for four more years (thanks to a fifth-year option), signing Jennings to a reasonable $15-20 million per year should not be prohibitive. The team should take the approach it did with Deommodore Lenoir this past season and get a deal done by December.
OT Colton McKivitz
Colton McKivitz is the starter at right tackle, but that is because the 49ers let Mike McGlinchey walk in free agency a few years ago. As a general approach, John Lynch does not spend a lot of capital—either in salary or draft picks—on offensive linemen. Last year, he allowed guard Aaron Banks and swing tackle Jaylon Moore to leave rather than pay the $9 million to Banks this year (which balloons to over $20 million in the following three years each) and $11 million to Moore (which swells to $18 million in 2026). Banks was an average starter, Moore an average backup, and the 49ers needed the cap space.
McKivitz should be viewed the same. Because tackles are highly coveted, he will receive offers far above his worth. If Moore, who was not a starter, garnered a contract worth $30 million, McKivitz will command more. A cheaper and more talented player could be had in the first two rounds of the draft.
DE Yetur Gross-Matos
Yetur Gross-Matos currently earns a little over $9 million per year. It is not a huge contract, but it is more than he has been worth so far, given his injuries last year. With the drafting of Mykel Williams and signing of Bryce Huff, unless Gross-Matos has a breakout year, he is not worth a large outlay of cash. If he stays healthy and proves to be a productive role player, the team should consider retaining him, but only at a role player's salary.
DT Jordan Elliott
Jordan Elliott was expected to provide strong run support last year, but he did anything but. It was a bit of a surprise he was not let go with the other players Lynch released this offseason. Though his salary is not a significant weight on the cap, it is still three times more than that of Evan Anderson, a young player with clear upside. The team should see if Elliott has a bounce-back year, but considering the draft capital they spent on the interior of the defensive line this spring, he should not feature into their long-term plans.
G Spencer Burford
A 4th-round pick in the 2022 draft, Spencer Burford has performed at a—well—4th-round level. He has started games but has been a liability in some of the biggest ones. He will make $3.5 million this year, but he is not worth that, and certainly not worth more. The 49ers should let him take his services elsewhere.
DE Sam Okuayinonu
Last year, the defensive line underperformed at a high level, which led to the purge of three starters this offseason. Sam Okuayinonu, however, was a pleasant surprise, posting 3 sacks in spot duty, suggesting he is worthy of a larger rotational role, someone to keep an eye on. An undrafted free agent from two years ago, he makes very little and is the kind of depth player teams need to keep starters fresh. He should be brought back on a similar deal or with a slight raise.
DT Kevin Givens
Kevin Givens is much like Okuayinonu, an undrafted free agent who produced a few sacks in spot duty. However, he entered the league in 2019 and is now 28, so we know his ceiling. If he'll sign for the veteran minimum, that's fine, but the team shouldn't do more than that.
On the horizon
There are two players who will become free agents in 2027 who are of consequence. The first is offensive tackle Trent Williams. Williams is in the last stage of his career. Turning 37 this month, he might retire when his contract is up, but he has said he has the desire—right now—to play until he is 40. He currently counts the most of any of the 49ers' players against the cap, and that number is scheduled to increase in 2026. He has been willing to restructure in the past, and the 49ers likely hope he will do so once more. However, his contract, health, and performance will be important to monitor.
Linebacker Dee Winters is in a make-or-break year. He started last year in place of Dre Greenlaw and played at an average level. That led Lynch to draft Nick Martin with the 75th pick this past spring. I am sure the team hopes Martin plays well enough to unseat Winters, but that is not a sure thing. Even if Martin does, though, Winters is a good player to have as a backup.
If he wins the starting job this year, Winters will go into his contract year, understandably believing he should be paid much more than backup money. Lynch should resist that and hope to bring him back as someone who provides bench strength.
Fortunately, the 49ers will go into next season without any drama on the horizon. They won't have any superstars who might be in a position to set the market. But these kinds of offseasons are often the ones that subtly set the tone for the salary cap down the road. Overspending on a few can limit the team's ability to sign a promising mid-range player later, and not paying a talented role player now can lead to losing someone who would have become a significant starter in a few years. Let's hope Lynch and company are shrewd in their planning.